WO2019156364A1 - Mask cleaning liquid composition - Google Patents

Abstract

A mask cleaning liquid composition according to the present invention is characterized by comprising: an amide-based compound represented by chemical formula 1; and an alkaline compound. The mask cleaning liquid composition according to the present invention has an advantage of exhibiting favorable cleaning power even without comprising an environmentally controlled substance, such as NMP.

Description

Mask Cleaning Liquid Composition

The present invention relates to mask cleaning liquid compositions, and in particular mask cleaning liquid compositions which facilitate the removal of various organics, in particular organic particles, on the mask used in the deposition process.

Flat panel displays (FPDs) are attracting attention as display devices, and among them, liquid crystal displays and organic light emitting diodes (OLEDs) are of interest.

Currently, the liquid crystal display device that is most used as a display has advantages such as light weight, small volume, and low power, compared to a conventional CRT (Cathode ray tube). However, since it is not self-luminous, the backlight should be used, and the viewing angle is limited by using liquid crystal.

On the other hand, OLED devices have advantages such as low voltage driving, high luminous efficiency, wide viewing angle, and fast response speed, and above all, they do not need back light because they are self-luminous. The OLED device emits light by recombining electrons and holes supplied from a cathode and an anode using a light emitting organic material that emits light.

A semiconductor device or a flat panel display such as an OLED may perform deposition of an organic material using a mask to form organic material layers such as various light emitting layers, hole injection layers, hole transport layers, electron transport layers, electron injection layers, and the like during the manufacturing process. At this time, the organic material is attached to the surface of the mask, the shape of the pattern formed by the mask may be deformed due to the organic material attached. This causes a decrease in the efficiency of the deposition process and may affect the performance of the semiconductor device or flat panel display to be manufactured, so it is necessary to remove the organic matter deposited on the mask.

Republic of Korea Patent Publication No. 2011-0095814 relates to a deposition material cleaning liquid composition and a cleaning method using the same, N-methyl-2-pyrrolidone (N-Methyl-2-pyrrolidone); And 1,3-dimethyl-2-imidazolidinone (1,3-Dimethyl-2-imidazolidinone).

Korean Patent No. 1388283 relates to a mask cleaning apparatus, comprising: an ultrasonic cleaner for generating ultrasonic waves to clean a mask immersed in a cleaning liquid; The ultrasonic cleaning unit includes a cleaning solution circulation unit for discharging and supplying the cleaning solution, and the ultrasonic waves in the ultrasonic cleaning unit have a frequency of 75 KHz or more and 90 KHz or less, the intensity is 800 W or more and 1100 W or less, and the cleaning solution is NMP (N-Methyl Pyrrolidinone). N-methylpyrrolidinone) is disclosed as a mask cleaning device characterized in that the mixture.

However, N-methyl-2-pyrrolidone (NMP), which is used in mask cleaning liquids in the related art, is a toxic substance. Specifically, according to the National Institute of Environmental Research, 2014-25, it is a substance classified as a toxic substance when 0.3 wt% or more is contained. The use of a mask cleaning liquid containing NMP is not only harmful to the human body but also bad for the environment.

In addition, the mask cleaning process should not degrade performance after long-term storage in the standby state because the operating time is determined according to the manufacturing process conditions. In particular, due to exposure to the atmosphere, there should be no degradation in water absorption.

On the other hand, the use of organic particles to improve the performance when forming the organic layer, such as the light emitting layer, hole injection layer, hole transport layer, electron transport layer, electron injection layer, etc. described above, these organic particles are mostly insoluble The problem arises that it is not easy to clean because of the bet.

Therefore, it does not contain environmental regulatory substances such as NMP, but also has excellent cleaning power, in particular, excellent cleaning power for organic particles, no performance degradation due to moisture absorption, and development of a mask cleaning liquid that is easy to process operation is required. have.

[Preceding technical literature]

[Patent Documents]

(Patent Document 1) Republic of Korea Patent Publication No. 2011-0095814 (2011.08.25.)

(Patent Document 2) Republic of Korea Patent No. 1388283 (2014.04.16.)

It is an object of the present invention to provide a mask cleaning liquid composition which exhibits good cleaning power, in particular, good cleaning power with respect to organic particles, without including environmental regulatory substances.

In addition, it is an object of the present invention to provide a cleaning liquid composition which is easy to process operation due to excellent stability and ultrasonic and electrolytic cleaning is unnecessary.

The present invention is an amide compound represented by the formula (1); And it provides a mask cleaning liquid composition comprising an alkaline compound.

[Formula 1]

In Chemical Formula 1,

R1 and R2 are each independently hydrogen, a methyl group or an ethyl group,

R3 is hydrogen; Or a C1 to C4 saturated or C2 to C4 unsaturated hydrocarbon group unsubstituted or substituted with a C1 to C4 alkoxy group,

Provided that when R1 and R2 are methyl groups,

R 3 is a C 2 to C 4 saturated or unsaturated hydrocarbon group unsubstituted or substituted with a C 1 to C 4 alkoxy group.

The mask cleaning liquid composition according to the present invention can exhibit good cleaning power, in particular, good cleaning power with respect to organic particles, without including an environmental regulation material such as NMP, and thus has an advantage of easy process operation.

In addition, the mask cleaning liquid composition according to the present invention has the advantage that the performance degradation due to moisture absorption is suppressed.

In addition, when the mask is cleaned using the mask cleaning liquid composition according to the present invention, ultrasonic and electrolytic cleaning are unnecessary.

Hereinafter, the present invention will be described in more detail.

In the present invention, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

In the present invention, when a part "includes" a certain component, this means that it may further include other components, without excluding the other components unless otherwise stated.

One embodiment of the present invention, the amide compound represented by the formula (1); And a mask cleaning liquid composition containing an alkaline compound.

[Formula 1]

In Chemical Formula 1,

R1 and R2 are each independently hydrogen, a methyl group or an ethyl group,

R3 is hydrogen; Or a C1 to C4 saturated or C2 to C4 unsaturated hydrocarbon group unsubstituted or substituted with a C1 to C4 alkoxy group,

Provided that when R1 and R2 are methyl groups,

R 3 is a C 2 to C 4 saturated or unsaturated hydrocarbon group unsubstituted or substituted with a C 1 to C 4 alkoxy group.

In the present invention, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C4. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy and the like, but is not limited thereto.

In the present invention, the saturated hydrocarbon group may be any of linear or branched chain and cyclic group that satisfy the carbon number.

As said linear or branched saturated hydrocarbon group, linear alkyl groups, such as a methyl group, an ethyl group, a propyl group, a butyl group; Branched alkyl groups, such as an isopropyl group and an isobutyl group, etc. are mentioned. The saturated hydrocarbon group is preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms. However, when both R1 and R2 are methyl groups, the saturated hydrocarbon group has 2 to 4 carbon atoms.

Cyclopropyl group, cyclobutyl group, etc. are mentioned as said cyclic saturated hydrocarbon group.

In the present invention, the unsaturated hydrocarbon group has an unsaturated group at the terminal, and may be a C 2 to C 4 linear aliphatic unsaturated hydrocarbon group or a branched aliphatic hydrocarbon group. Examples of the linear aliphatic unsaturated hydrocarbon group include vinyl group, propenyl group (allyl group) and butynyl group. Examples of the branched aliphatic unsaturated hydrocarbon group include 1-methylpropenyl group and 2-methylpropenyl group. However, it is not limited thereto.

In one embodiment of the present invention, the amide compound represented by Formula 1 is N, N-dimethylpropionamide, N, N-dimethylisobutylamide, N, N-dimethylacrylamide, N, N-dimethylmetha Krillamide, N-ethylformamide, N, N-diethylformamide, N, N-diethylacetamide, N, N-diethylpropionamide, N, N-diethylisobutylamide, N, N- It may be at least one selected from the group consisting of diethylacrylamide, N, N-diethyl methacrylamide, 3-methoxy-N, N-dimethylpropionamide and 3-butoxy-N, N-dimethylpropionamide. .

Since the mask cleaning liquid composition according to the present invention includes the amide-based compound represented by Chemical Formula 1, the mask cleaning liquid composition is excellent in mask cleaning power, and does not cause damage to materials such as SUS and Invar forming a mask, for example, NMP. Because it can be used instead of environmentally harmful substances such as environmentally friendly and has an easy advantage in terms of process. Specifically, the mask cleaning liquid composition according to the present invention does not cause damage such as corrosion, such as a mask of Invar material used to form the organic light emitting device and a stainless steel (SUS 304, 316, 420, etc.) supporting the mask. There is this.

The amide compound represented by Chemical Formula 1 may be included in an amount of 50 to 99.9 parts by weight, preferably 60 to 98 parts by weight, and more preferably 75 to 95 parts by weight, based on 100 parts by weight of the mask cleaning liquid composition. There is an advantage that the solvent and cleaning ability to the organic light emitting material is excellent.

In short, the mask cleaning liquid composition according to the present invention is excellent in cleaning power for various organic substances adhered to the mask.

The organic material may be, for example, a material forming an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), or the like that emits red, green, and / or blue light. The emission layer may emit red, green, and / or blue, and may be formed of a phosphor or a fluorescent material. The light emitting host material may be CBP ((carbazole-9-yl) biphenyl), BSBF (2- (9,9-Spirobifluoren-2-yl) -9,9-spirobifluorene), biphenyl-3,3'-diyl ) bis (diphenylphosphine oxide) (BiPh-m-BiDPO), or mCP (1,3-bis (carbazol-9-yl)) may be used, but is not limited thereto.

Red luminescent dopants include PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonate iridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium), PtOEP (octaethylporphyrin platinum Phosphors such as), fluorescent materials such as tris- (8-hydroxyquinoline) aluminum), and the like may be used.

As the green light emitting dopant, a phosphor such as Ir (ppy) ₃ (fac tris (2-phenylpyridine) iridium) or a fluorescent material such as Alq3 (tris- (8-hydroxyquinoline) aluminum) may be used, but is not limited thereto. no.

Examples of blue light emitting dopants include phosphors such as (4,6-F ₂ ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, ditylbenzene (DSB), distriarylene (DSA), PFO-based polymers, and PPV. Fluorescent materials such as polymers may be used, but are not limited thereto.

The hole transport layer is NPD (N, N'-Di (1-naphthyl) -N, N ''-diphenyl- (1,1'-biphenyl) -4,4'-diamine), TPD (N, N'-bis -(3-methylphenyl) -N, N'-bis- (phenyl) -benzidine), s-TAD and MTDATA (4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenyl-amino)- triphenylamine), but is not limited thereto, such as triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkaine derivatives, pyrazoline derivatives and pyrazolone derivatives, for example, as a hole transport layer material. , Phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane-based, aniline-based aerials Copolymers, conductive polymer oligomers (particularly thiophene oligomers) and the like.

In addition, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and 3- (6-diphenylphosphinylnaphth included in the hole blocking layer -2-yl) -1,10-phenanthroline (Phen-m-PhDPO), aluminum complex, etc. can be used, and CuPc (copper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene) as the material of the hole injection layer , At least one selected from the group consisting of PANI (polyaniline) and NPD, Bis [2- (2-pyridinyl-N) phenyl-C] (2,4-pentanedionato-O2 as a material of a capping layer (CPL) , O4) iridium (III) and the like can be used.

The mask cleaning liquid composition according to the present invention comprises an alkaline compound, and since the mask cleaning liquid composition according to the present invention includes the above-mentioned amide compound and an alkaline compound, various organic substances attached to the mask, in particular, in the form of organic particles, are fired. There is an advantage that the cleaning of the soluble organic material is easy.

Although not wishing to be bound by theory, the alkaline compound is insoluble in the form of a metal complex due to the action of raising the pH in the solution to lift off the adsorbed organic material. Organic materials such as Bis [2- (2-pyridinyl-N) phenyl-C] (2,4-pentanedionato-O2, O4) iridium (III), Poly (9,9-dioctylfluorene-alt-N- (4- It is easy to clean insoluble organic materials such as sec-butylphenyl) -diphenylamine).

In another embodiment of the present invention, the alkaline compound may include at least one selected from the group consisting of an inorganic base and an organic base.

The inorganic base may include, for example, ammonium hydroxide, sodium hydroxide, potassium hydroxide, and the like, but is not limited thereto, and inorganic bases commonly used in the art may be used without limitation as long as the object of the present invention is not impaired.

The organic base may be, for example, primary amines such as methyl amine, ethylamine, isopropyl amine, monoisopropylamine and the like; Secondary amines such as diethyl amine, diisopropyl amine and dibutylamine; Tertiary amines such as trimethylamine, triethylamine, triisopropylamine and tributylamine; Quaternary amines such as tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide; Choline, monoethanolamine, diethanol amine, 2-amino ethanol, 2- (ethyl amino) ethanol, 2- (methyl amino) ethanol, N-methyl diethanol amine, dimethylaminoethanol, diethylaminoethanol, nitrilotriethanol , Alkanolamines such as 2- (2-aminoethoxy) ethanol, 1-amino-2-propanol, triethanolamine, monopropanolamine, dibutanolamine, and the like, and these may be used alone or in combination of two or more thereof. have.

In another embodiment of the present invention, the organic base may include an amine compound. Specifically, in the case of washing insoluble light emitting particles including organic and inorganic substances, it is preferable to use an amine compound having a hydroxyl group in order to prevent resorption phenomenon after the cleaning is completed.

In still another embodiment of the present invention, the alkaline compound may be included in an amount of 0.05 to 10 parts by weight, preferably 1 to 7 parts by weight, based on 100 parts by weight of the mask cleaning liquid composition. In this case, there is an advantage of maximizing the removal of the insoluble organic particles, it is possible to suppress the phenomenon that the dissolving power and detergency for the organic light emitting material is reduced by reducing the content of the amide compound relatively.

In another embodiment of the present invention, the mask cleaning liquid composition may further comprise a water-soluble polar solvent.

In still another embodiment of the present invention, the water-soluble polar solvent may include one or more selected from the group consisting of a proton polar solvent and an aprotic polar solvent.

Specifically, the water-soluble polar solvent according to the present invention may include a proton polar solvent and an aprotic polar solvent, and these may be used alone or in combination.

The proton polar solvent is, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono Isopropyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monoisopropyl ether, triethylene glycol monobutyl ether, polyethylene glycol monomethyl ether, polyethylene glycol monobutyl Alkylene glycol monoalkyl ethers such as ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether; And tetrahydrofurfuryl alcohol; And 4-hydroxymethyl-1,3-dioxolane, 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane, 4-hydroxyethyl-2,2-dimethyl- and the like. 1,3-dioxolane, 4-hydroxypropyl-2,2-dimethyl-1,3-dioxolane, 4-hydroxybutyl-2,2-dimethyl-1,3-dioxolane, 4-hydroxymethyl Hydroxydioxolane compounds such as -2,2-diethyl-1,3-dioxolane and 4-hydroxymethyl-2-methyl-2-ethyl-1,3-dioxolane; One or two or more species may be used together, but is not limited thereto, and a quantum polar solvent may be used that does not impair the object of the present invention.

The aprotic polar solvents include, for example, N, N-dimethylpropionamide (DMPA), N, N-dimethylisobutylamide (DMIB), N, N-dimethylacrylamide (DMAR), N, N-dimethylmethacrylamide, N, N-diethylformamide, N, N-diethylacetamide (DEAC), N, N-diethylpropionamide, N, N-diethylisobutylamide, N, N-diethylacrylamide, N , N-diethylmethacrylamide, 3-methoxy-N, N-dimethylpropionamide (MDMP) and 3-butoxy-N, N-dimethylpropionamide, N, N-diethylformamide (DEF), Dialkylamide compounds such as N, N-dimethylformamide (DMF); Mono such as N-methylformamide (NMF), N-methylpropionamide (NMPA), N-methylacetamide (NMA), N-ethylacetamide (NEA), and N- (2-hydroxyethyl) acetamide Amide compounds; lactone compounds such as γ-butyrolactone; Sulfoxide compounds such as dimethyl sulfoxide (DMSO) and sulfolane; Phosphate compounds such as triethyl phosphate (TEP) and tributyl phosphate (TBP); Carbonate compounds, such as dimethyl carbonate (DMC), ethylene carbonate (EC), and propylene carbonate (PC), are mentioned, These can be used individually or in mixture of 2 or more types, It is not limited to this also.

Preferably, an amide compound such as a dialkylamide compound or a monoamide compound, and more preferably a dialkylamide compound is preferable in view of washability.

The water-soluble polar solvent plays a role of dissolving the organic material remaining in the mask together with the amide compound and the alkaline compound represented by the formula (1), and also facilitates the removal of the cleaning solution by water in the rinse process of deionized water after washing. By minimizing the resorption / reattachment of the removed organic material or may play a role in improving the removal power of a specific organic material.

The water-soluble polar solvent may be selected according to the performance required in the subsequent cleaning process, it is preferable that the water-soluble polar solvent does not have a low boiling point for proper cleaning power and stable operation of the process. For example, it is preferable to have a boiling point of 150-290 degreeC. When using a water-soluble polar solvent having a boiling point within the above range it may be preferable in terms of environmental and process. Specifically, it is preferable because it is volatilized in the washing step, the amount of the process used increases, and the phenomenon which adversely affects the working environment can be suppressed.

In another embodiment of the present invention, the water-soluble polar solvent may be included in 5 to 35 parts by weight, preferably 5 to 30 parts by weight, more preferably 10 to 20 parts by weight based on 100 parts by weight of the total cleaning liquid composition. have. When the water-soluble polar solvent is included in the above range, it is preferable because there is an advantage in that the cleaning liquid composition can be prepared excellent in cleaning power and easy to remove the cleaning liquid by water in the rinsing process of deionized water after washing.

In another embodiment of the present invention, the mask cleaning liquid composition may contain 5 parts by weight or less based on 100 parts by weight of the total.

The water may be included in an amount of preferably 3 parts by weight or less based on 100 parts by weight of the mask cleaning solution composition.

When the water is included below the above range it is preferable not to cause a reduction in the removal of organic EL (Organic Electro Luminescence).

The water may be deionized water (DIW) or ultrapure water in which impurities are reduced as much as possible, but are not limited thereto.

In addition, the water may be included by absorbing moisture over time, it is preferable that the cleaning liquid composition according to the present invention does not contain water.

Since the cleaning liquid composition according to the present invention has excellent cleaning power, including the amide compound and the alkaline compound represented by Chemical Formula 1, ultrasonic cleaning and electrolytic cleaning are unnecessary.

In still another embodiment of the present invention, the mask cleaning liquid composition may be a mask cleaning liquid composition for cleaning a mask used in an organic material vacuum deposition process.

The mask cleaning liquid composition according to the present invention has an advantage of excellent cleaning power without including environmental regulatory substances such as NMP, DMF, DMAC, and NMF.

Hereinafter, the present invention will be described in detail with reference to Examples. However, the embodiments according to the present disclosure may be modified in various other forms, and the scope of the present specification is not to be interpreted as being limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art. In addition, "%" and "part" which show content below are a basis of weight unless there is particular notice.

Example  And Comparative example : Preparation of Cleaning Liquid Composition

To prepare a cleaning solution composition according to the Example and Comparative Example according to the configuration and composition of Table 1.

division	Amide compound		Alkali compounds		Quantum polar solvent		Etc
	designation	[weight%]	designation	[weight%]	designation	[weight%]	designation	[weight%]
Example 1	DMPA	90	NMEA	10	-	-	-	-
Example 2	DMPA	89	NMEA	10			H 2 O	One
Example 3	DMPA	87	NMEA	10			H 2 O	3
Example 4	DMPA	85	NMEA	10	-	-	H 2 O	5
Example 5	DMPA	83	NMEA	10			H 2 O	7
Example 6	DMPA	99.9	KOH	0.1	-	-	-	-
Example 7	DMPA	96	TMAH	One	-	-	H 2 O	3
Example 8	DMAC	90	MEA	10	-	-	-	-
Example 9	DMAC	99.9	MEA	0.1	-	-	-	-
Example 10	DMAC	98.9	MEA	0.1	-	-	H 2 O	One
Example 11	DMF	90	NMEA	10	-	-	-	-
Example 12	DMF	99.9	NMEA	0.1	-	-	-	-
Example 13	NMF	90	MEA	10	-	-	-	-
Example 14	NMF	99.9	NaOH	0.1	-	-	-	-
Example 15	DMPA	80	NMEA	5	DEDG	15	-	-
Example 16	DMPA	79.5	NMEA	5	DEDG	15	H 2 O	0.5
Example 17	DMPA	75	NMEA	5	DEDG	15	H 2 O	5
Example 18	DMPA	60	NMEA	10	DEDG	30	-	-
Example 19	DMPA	60	NMEA	10	DEDG	23	H 2 O	7
Example 20	DMPA	94	KOH	One	MEDG	5	-	-
Example 21	DMAC	80	MEA	5	DMI	15	-	-
Example 22	DMF	60	NMEA	10	EDG	30	-	-
Example 23	DMPA	80	TMAH	One	DEDG	15	H 2 O	4
Comparative Example 1	DMDA	100	-	-	-	-	-	-
Comparative Example 2	DMPA	50	-	-	DMTG	50	-	-
Comparative Example 3	-	-	NaOH	100	-	-	-	-
Comparative Example 4	-	-	MEA	100	-	-	-	-
Comparative Example 5	-	-	NMEA	100	-	-	-	-
Comparative Example 6	-	-	DGA	100	-	-	-	-
Comparative Example 7	-	-	AEEA	100	-	-	-	-
Comparative Example 8	-	-	NMEA	50	EDG	50	-	-
Comparative Example 9	-	-	KOH	30	DMI	70	-	-
Comparative Example 10	-	-	-	-	DEDG	100	-	-
Comparative Example 11	-	-	-	-	MDG	100	-	-
Comparative Example 12	-	-	-	-	DMI	100	-	-
Comparative Example 13	-	-	-	-	EDG	100	-	-
Comparative Example 14	-	-	-	-	DMDG	100	-	-
Comparative Example 15	-	-	-	-	DMTG	100	-	-

Experimental Example  1: Solubility evaluation of organic light emitting device

In order to confirm the cleaning effect of the mask cleaning liquid compositions according to the Examples and Comparative Examples, four masks in which the organic material used as the light emitting layer and the electron / hole transporting layer included in the organic light emitting device are separately adsorbed according to a conventional deposition process ( Material: Invar) was evaluated for solubility.

After separating the organic material from the mask after the deposition process, using a mortar and pestle to form a powder, separated into a 224㎛ sieve. After dissolving the powder at room temperature using a 50 ml beaker of 0.015% organic material by weight of the prepared mask cleaning liquid composition, the solubility (powder melting rate, minute unit measurement) of the mask cleaning liquid composition (chemical solution) according to Examples and Comparative Examples was measured. The evaluation is shown in Table 2 below.

division	Solubility Assessment
	Mask 1 separated organic material	Mask 2 separated organic material	Mask 3 separated organic material	Mask 4 separated organic materials
Example 1	6 minutes	6 minutes	25 minutes	Insoluble
Example 2	6 minutes	6 minutes	25 minutes	Insoluble
Example 3	6 minutes	6 minutes	25 minutes	Insoluble
Example 4	6 mins	7 mins	27 mins	Insoluble
Example 5	7 mins	8 mins	31 minutes	Insoluble
Example 6	6 minutes	6 minutes	28 minutes	Insoluble
Example 7	6 minutes	6 mins	30 minutes	Insoluble
Example 8	6 mins	6 mins	35 mins	Insoluble
Example 9	7 mins	5 minutes	30 minutes	Insoluble
Example 10	7 mins	5 minutes	31 mins	Insoluble
Example 11	8 mins	8 mins	30 minutes	Insoluble
Example 12	8 mins	8 mins	30 minutes	Insoluble
Example 13	7 mins	10 minutes	40 mins	Insoluble
Example 14	9 mins	10 minutes	40 mins	Insoluble
Example 15	6 mins	4 mins	15 mins	Insoluble
Example 16	6 mins	4 mins	15 mins	Insoluble
Example 17	6 mins	5 minutes	17 mins	Insoluble
Example 18	4 mins	6 mins	20 minutes	Insoluble
Example 19	6 mins	7 mins	23 mins	Insoluble
Example 20	6 minutes	8 mins	22 mins	Insoluble
Example 21	5 minutes	5 minutes	21 mins	Insoluble
Example 22	10 minutes	10 minutes	25 mins	Insoluble
Example 23	5 minutes	5 minutes	18 mins	Insoluble
Comparative Example 1	45 mins	60 mins	120 minutes	Insoluble
Comparative Example 2	25 mins	20 minutes	60 mins	Insoluble
Comparative Example 3	55 mins	55 mins	100 mins	Insoluble
Comparative Example 4	50 minutes	50 minutes	120 minutes	Insoluble
Comparative Example 5	55 mins	55 mins	120 minutes	Insoluble
Comparative Example 6	120 minutes	120 minutes	180 minutes	Insoluble
Comparative Example 7	80 minutes	80 minutes	140 minutes	Insoluble
Comparative Example 8	60 mins	60 mins	120 minutes	Insoluble
Comparative Example 9	40 mins	40 mins	100 mins	Insoluble
Comparative Example 10	25 mins	30 minutes	100 mins	Insoluble
Comparative Example 11	30 minutes	25 mins	120 minutes	Insoluble
Comparative Example 12	35 mins	40 mins	65 minutes	Insoluble
Comparative Example 13	40 mins	45 mins	80 minutes	Insoluble
Comparative Example 14	45 mins	50 minutes	85 minutes	Insoluble
Comparative Example 15	50 minutes	50 minutes	120 minutes	Insoluble
Mask 1 adsorbent: 2- (9,9-Spirobifluoren-2-yl) -9,9-spirobifluorene (BSBF), mask 2 adsorbent: biphenyl-3,3'-diyl) bis (diphenylphosphine oxide) (BiPh- m-BiDPO), Mask 3 adsorbent: 3- (6-diphenylphosphinylnaphth-2-yl) -1,10-phenanthroline (Phen-m-PhDPO), Mask 4 adsorbent: Bis [2- (2-pyridinyl-N ) phenyl-C] (2,4-pentanedionato-O2, O4) iridium (III)

Experimental Example  2: organic of cleaning liquid particle Removability  evaluation

In order to confirm the cleaning effect of the mask cleaning liquid compositions according to the Examples and Comparative Examples, four masks in which the organic material used as the light emitting layer and the electron / hole transporting layer included in the organic light emitting device are separately adsorbed according to a conventional deposition process ( Material: Invar) was evaluated to remove the organic particles of the cleaning liquid.

In order to confirm the organic particle removal effect of the cleaning liquid composition, after separating the organic material from the mask after the deposition process, in the same manner as in Experimental Example 1 to make a powder form using a pestle of the mask cleaning liquid composition of 0.05% by weight The organic material was uniformly dispersed in NMP using a sonicator for 1 hour, dropped onto 1.5 × 1.5 Invar, and dried in an oven at 100 ° C. for 1 hour. The substrate was immersed in each composition (chemical liquid) for 20 seconds at room temperature, and then washed and evaluated by visual evaluation and an optical microscope. The results are shown in Table 3 below. When visually observed, very good is indicated by ◎, good is ○, usually △, and no as ×.

division	Cleaning power
	Mask 1 separated organic material	Mask 2 separated organic material	Mask 3 separated organic material	Mask 4 separated organic materials
Example 1	◎	◎	○	◎
Example 2	◎	◎	○	◎
Example 3	◎	◎	○	◎
Example 4	◎	◎	○	○
Example 5	◎	○	○	○
Example 6	◎	◎	○	○
Example 7	◎	◎	◎	○
Example 8	◎	◎	◎	○
Example 9	◎	○	○	○
Example 10	◎	○	○	○
Example 11	◎	○	○	◎
Example 12	◎	○	○	○
Example 13	◎	○	◎	○
Example 14	◎	○	○	○
Example 15	◎	◎	◎	◎
Example 16	◎	◎	◎	◎
Example 17	◎	◎	◎	○
Example 18	◎	◎	◎	◎
Example 19	◎	◎	◎	○
Example 20	◎	◎	◎	◎
Example 21	◎	◎	◎	○
Example 22	○	○	○	◎
Example 23	◎	◎	◎	◎
Comparative Example 1	○	△	△	△
Comparative Example 2	○	○	△	△
Comparative Example 3	△	△	△	△
Comparative Example 4	△	△	×	×
Comparative Example 5	△	△	x	×
Comparative Example 6	x	x	x	×
Comparative Example 7	△	△	x	×
Comparative Example 8	x	x	x	×
Comparative Example 9	x	△	△	×
Comparative Example 10	○	○	△	×
Comparative Example 11	△	△	×	×
Comparative Example 12	△	×	×	×
Comparative Example 13	×	×	×	×
Comparative Example 14	×	×	×	×
Comparative Example 15	×	×	×	×
Mask 1 adsorbent: 2- (9,9-Spirobifluoren-2-yl) -9,9-spirobifluorene (BSBF), mask 2 adsorbent: biphenyl-3,3'-diyl) bis (diphenylphosphine oxide) (BiPh- m-BiDPO), Mask 3 adsorbent: 3- (6-diphenylphosphinylnaphth-2-yl) -1,10-phenanthroline (Phen-m-PhDPO), Mask 4 adsorbent: Bis [2- (2-pyridinyl-N ) phenyl-C] (2,4-pentanedionato-O2, O4) iridium (III)

Looking at Examples 1 to 20 and Comparative Examples 3 to 15 in Table 2, when the amide compound represented by Formula 1 is included, it can be confirmed that the solvent 1 to 3 has excellent solubility in the adsorbent. Comparing Examples 1 to 20 and Comparative Examples 1 and 2 in Table 3, it can be seen that excellent cleaning power can be obtained when an alkaline compound is included, and the comparative example does not include the amide series represented by Formula 1 It can be seen that the removal is not excellent.

Claims (10)

1. Amide-based compounds represented by the formula (1); And

   Mask cleaning liquid composition comprising an alkaline compound:

   [Formula 1]

   

   In Chemical Formula 1,

   R1 and R2 are each independently hydrogen, a methyl group or an ethyl group,

   R3 is hydrogen; Or a C1 to C4 saturated or C2 to C4 unsaturated hydrocarbon group unsubstituted or substituted with a C1 to C4 alkoxy group,

   Provided that when R1 and R2 are methyl groups,

   R 3 is a C 2 to C 4 saturated or unsaturated hydrocarbon group unsubstituted or substituted with a C 1 to C 4 alkoxy group.
2. The method of claim 1,

   Amide-based compound represented by Formula 1 is N, N-dimethylpropionamide, N, N-dimethylisobutylamide, N, N-dimethylacrylamide, N, N-dimethylmethacrylamide, N-ethylformamide, N, N-diethylformamide, N, N-diethylacetamide, N, N-diethylpropionamide, N, N-diethylisobutylamide, N, N-diethylacrylamide, N, N- A mask cleaning liquid composition which is at least one selected from the group consisting of diethyl methacrylamide, 3-methoxy-N, N-dimethylpropionamide and 3-butoxy-N, N-dimethylpropionamide.
3. The method of claim 1,

   The alkaline compound is a mask cleaning liquid composition comprising at least one selected from the group consisting of an inorganic base and an organic base.
4. The method of claim 3,

   The organic base is a mask cleaning liquid composition comprising an amine compound.
5. The method of claim 1,

   Mask cleaning liquid composition further comprising a water-soluble polar solvent.
6. The method of claim 5,

   The water-soluble polar solvent is a mask cleaning liquid composition comprising at least one selected from the group consisting of a protic polar solvent and an aprotic polar solvent.
7. The method of claim 1,

   The mask cleaning liquid composition comprising less than 5 parts by weight of water based on 100 parts by weight of the total.
8. The method of claim 1,

   The alkaline compound is a mask cleaning liquid composition that is contained in 0.05 to 10 parts by weight based on 100 parts by weight of the total mask cleaning liquid composition.
9. The method of claim 5,

   The water-soluble polar solvent is a mask cleaning liquid composition comprising 5 to 35 parts by weight based on 100 parts by weight of the total mask cleaning liquid composition.
10. The method of claim 1,

    The mask cleaning liquid composition is to clean the mask used in the organic material vacuum deposition process.